When confronted with the problems of urban school districts, such as an ever-increasing achievement gap, the underfunding of school districts, increased shortages of qualified teachers, greater emphasis on accountability, and the loss of public confidence, African American superintendents have considerable difficulty leading their school districts. This article begins with a discussion of urban school district funding disparities and their impact on district operations. The article then discusses stakeholder expectations and how they affect the job performance of these superintendents. The text also describes what politicians, school boards, the media, parents, community members, and school district staff want superintendents to do and how they make it difficult for them to meet these goals. In addition, the article discusses recent changes that could serve as a harbinger of the future regarding the racial composition of superintendents in both traditional settings and reformed school districts.